A former FBI informant suspected of leading the largest prostitution ring in San Antonio since the infamous madam Theresa Brown case of the 1980s has been arrested on federal drug distribution charges.

Samuel “Sammy” Flores Jr., 43, was nabbed this week in Austin on an indictment alleging he was dealing methamphetamine in San Antonio. He was denied bond during a hearing in Austin on Thursday, and ordered transferred to San Antonio for trial.

Flores also was investigated in 2007 by the San Antonio Police Department. During that time, a raid of his alleged business, Executive Playmates, drew headlines and was the lead story on local TV news reports. The case, however, never was prosecuted.

Executive Playmates was suspected by SAPD of generating about $150,000 a month from prostitution between 2005 and 2007.

Run mostly from a middle-class neighborhood on Callaghan Road near Vance Jackson, the service advertised in the Yellow Pages and online and reportedly employed 300 women who serviced 2,000 clients.

Police Chief William McManus never publicly identified the operators, and he and then-City Attorney Michael Bernard refused to release the client list or records related to people who used Executive Playmates' services.

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“We've got men who spent over $15,000 on escorts in a six-month period,” one law enforcement source told the San Antonio Express-News in 2007, while another said, “It was a multimillion-dollar business.”

Other documents obtained by the Express-News through open-records requests identify Flores as the operator of Executive Playmates and said he was the investigation's main target.

The federal prostitution/money laundering case fizzled amid allegations from some who alleged the FBI interfered with the SAPD probe, and that Flores was protected because he cooperated with the FBI on unrelated investigations.

The FBI and U.S. attorney's office denied the allegations, but nonetheless, the matter bruised feelings between the FBI and SAPD and resulted in an internal affairs investigation by the FBI's Office of Professional Responsibility.

FBI headquarters refused the newspaper's requests to release its findings.

In the latest case, Flores was indicted in February along with Catalina Davis, who was caught with methamphetamine at her Barrington Street apartment during a raid by SAPD's gang unit.

She pleaded guilty Sept. 30 to conspiracy to possess with intent to distribute methamphetamine and to aiding and abetting. She admitted getting 2 ounces of the drug from Flores, her plea documents show.

Like Flores, she faces up to 40 years in federal prison. She is scheduled for sentencing in January.

Flores is the son of the late Samuel Flores Sr., a marijuana-smuggling kingpin in the 1970s and 1980s before he was gunned down at a roadblock in Guadalajara by Mexican police in October 1986. He'd been a fugitive from drug charges in the U.S. since 1981, newspaper reports at the time stated.

In January 1987, three months after his father's death, the younger Flores was caught at the airport in Pittsburgh, Pa., with $17,000 in cash and a .22-caliber pistol with a silencer.

Documents seized from him indicated he was involved in a 205-pound marijuana sale in Pittsburgh, newspaper stories at the time said. He returned to San Antonio with a sentence of probation after a plea deal.

His lawyer at the time, George Bills, said in an interview that the escort service venture wouldn't be out of the ordinary for Flores, given his lifestyle and the company he kept.

Flores didn't return messages seeking comment for this report. But several people familiar with Flores and his family spoke on condition of anonymity because they feared retribution.

“Sam was a high roller when he was 16, so that would fit,” Bills said. “When he was here, he would just fly in. Some of the young ladies that came with him were attractive.”

In 1993, Flores was caught with a small load of marijuana in Shelby County, Tenn. He received two years of probation, but fled, court records show.

In 1994, he was arrested in San Antonio and charged in federal court in Pittsburgh after his mother, Isabel Flores, was arrested in Pennsylvania.

The woman sold more than 2 pounds of cocaine for $36,500 to an informant, court records and newspaper reports show. She began cooperating almost immediately and pleaded guilty to conspiring to distribute cocaine, the stories said.

Sammy Flores pleaded guilty to conspiring to distribute nearly 5 pounds of cocaine and several pounds of marijuana in Pittsburgh between July 1993 and July 1994. He told law officers his mother was his drug courier.

In 1995, he was sentenced to more than 10 years in federal prison.

But court records show he began to feed information to federal law officers while he was doing his stint in Texas and Louisiana.

In 2002, the government asked a judge to reduce his sentence. The judge agreed and released him Sept. 15, 2002, almost three years early, court records show.

The judge ordered Flores to remain under federal supervision for five years. The supervision was transferred to San Antonio in 2003, court records show. It still was in place while Executive Playmates was under investigation from 2005 through 2007, records show.

Theresa Brown, meanwhile, ran a brothel on the North Side that attracted 3,000 customers including politicians, athletes and lawyers until it was raided in 1981. She died Sept. 18, 2012, of natural causes.

San Antonio police, acting under a court order in 1985, torched the client list they confiscated from her bordello at 315 Northtrail Drive, but the whereabouts of her back-up list, which was the subject of a First Amendment court battle, remains unknown.